Condensed cyclic compound and organic light emitting device including the same

ABSTRACT

A condensed cyclic compound represented by Formula 1: 
                         
wherein in Formula 1, groups and variables are the same as defined in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application No.10-2014-0143686, filed on Oct. 22, 2014, in the Korean IntellectualProperty Office, and all the benefits accruing therefrom under 35 U.S.C.§ 119, the content of which is incorporated herein in its entirety byreference.

BACKGROUND

1. Field

The present disclosure relates to a condensed cyclic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs exhibit excellent luminance, drivingvoltage, and response speed characteristics, and produce full-colorimages.

A typical organic light-emitting device includes an anode, a cathode,and an organic layer that is disposed between the anode and the cathodeand includes an emission layer. A hole transport region may be disposedbetween the anode and the emission layer, and an electron transportregion may be disposed between the emission layer and the cathode. Holesprovided from the anode may move toward the emission layer through thehole transport region, and electrons provided from the cathode may movetoward the emission layer through the electron transport region. Theholes and the electrons are recombined in the emission layer to produceexcitons. These excitons change from an excited state to a ground state,thereby generating light.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Provided are a condensed cyclic compound and an organic light-emittingdevice including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented exemplary embodiments.

According to an exemplary embodiment, a condensed cyclic compoundrepresented by Formula 1 is provided:

wherein in Formulae 1 and 2,

ring A₁ is selected from a substituted or unsubstituted 5-memberedcarbocyclic group, a substituted or unsubstituted 6-membered carbocyclicgroup, a substituted or unsubstituted 5-membered heterocyclic group, anda substituted or unsubstituted 6-membered heterocyclic group, whereinthe substituted or unsubstituted 5-membered heterocyclic group and thesubstituted or unsubstituted 6-membered heterocyclic group includes aheteroatom selected from the group consisting of O, S, and N(R₉), n isan integer selected from 0 to 5, provided that when n is 2 or more, ringA₁ are identical to or different from each other,

X₁ is N, C(R₁), or C,

X₂ is N, C(R₂), or C,

X₃ is N, C(R₃), or C,

X₄ is N, C(R₄), or C,

X₅ is N or C(R₅),

X₆ is N or C(R₆),

X₇ is N or C(R₇),

X₈ is N or C(R₈),

provided that

when X₁ is C, X₁ is linked to (L₁)_(a1), (L₂)_(a2), or (L₃)_(a3),

when X₂ is C, X₂ is linked to (L₁)_(a1), (L₂)_(a2), or (L₃)_(a3),

when X₃ is C, X₃ is linked to (L₁)_(a1), (L₂)_(a2), or (L₃)_(a3),

when X₄ is C, X₄ is linked to (L₁)_(a1), (L₂)_(a2), or (L₃)_(a3),

at least one selected from X₁ to X₄ is C, and

at least one selected from X₁ to X₈ is N,

L₁ to L₃ are each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₁₄arylene group, a substituted or unsubstituted C₁-C₁₃ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

a1 to a3 are each independently 0, 1, or 2,

R₁ to R₉ and R₁₁ to R₁₃ are each independently selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₁₄ aryl group, a substituted or unsubstituted C₆-C₁₄aryloxy group, a substituted or unsubstituted C₆-C₁₄ arylthio group, asubstituted or unsubstituted C₁-C₁₃ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇),

wherein R₁₄ to R₁₆ are each independently a group represented by Formula2,

b1, b3, c1, and c3 are each independently an integer selected from 1 to4, b2 and c2 are each independently an integer selected from 0 to 3, andc1+c2+c3≥1,

at least one of substituents of the substituted 5-membered carbocyclicgroup, substituted 6-membered carbocyclic group, substituted 5-memberedheterocyclic group, substituted 6-membered heterocyclic group,substituted C₃-C₁₀ cycloalkylene group, substituted C₁-C₁₀heterocycloalkylene group, substituted C₃-C₁₀ cycloalkenylene group,substituted C₁-C₁₀ heterocycloalkenylene group, substituted C₆-C₁₄arylene group, substituted C₁-C₁₃ heteroarylene group, substituteddivalent non-aromatic condensed polycyclic group, substituted divalentnon-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₁₄ aryl group, substituted C₆-C₁₄ aryloxy group,substituted C₆-C₁₄ arylthio group, substituted C₁-C₁₃ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ arylgroup, a C₆-C₁₄ aryloxy group, a C₆-C₁₄ arylthio group, a C₁-C₁₃heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₄ alkyl group, a C₂-C₁₄alkenyl group, a C₂-C₁₄ alkynyl group, a C₁-C₁₃ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₆-C₁₄aryloxy group, a C₆-C₁₄ arylthio group, a C₁-C₁₃ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇); and

—N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, and Q₂₁ to Q₂₇ are each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₁-C₁₃heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

wherein the number of rings that are condensed with each other in thedivalent non-aromatic condensed polycyclic group, divalent non-aromaticcondensed heteropolycyclic group, monovalent non-aromatic condensedpolycyclic group, and monovalent non-aromatic condensed heteropolycyclicgroup is 2 or 3.

According to another exemplary embodiment, an organic light-emittingdevice includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and at least onecondensed cyclic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the FIGURES, to explain aspects. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “comprises” and/or“comprising,” or “includes” and/or “including” when used in thisspecification, specify the presence of stated features, regions,integers, steps, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,regions, integers, steps, operations, elements, components, and/orgroups thereof.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the FIGURES. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the FIGURES. For example, if the device in theFIGURES is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the exemplary term “below” can encompass both anorientation of above and below. The device may be otherwise oriented(rotated 90 degrees or at other orientations) and the spatially relativedescriptors used herein interpreted accordingly.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this invention belongs. It will befurther understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the relevant art and thepresent disclosure, and will not be interpreted in an idealized oroverly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

A condensed cyclic compound may be represented by Formula 1:

wherein R₁₄ to R₁₆ in Formula 1 may be each independently a grouprepresented by Formula 2. Formula 2 may be understood by referring tothe descriptions below.

In Formula 2, ring A₁ may be selected from a substituted orunsubstituted 5-membered carbocyclic group, a substituted orunsubstituted 6-membered carbocyclic group, a substituted orunsubstituted 5-membered heterocyclic group, and a substituted orunsubstituted 6-membered heterocyclic group, wherein the substituted orunsubstituted 5-membered heterocyclic group and the substituted orunsubstituted 6-membered heterocyclic group may be selected from thegroup consisting of O, S, and N(R₉).

In some embodiments, ring A₁ in Formula 2 may be selected from

a 5-membered carbocyclic group, a 6-membered carbocyclic group, a5-membered heterocyclic group, and a 6-membered heterocyclic group; and

a 5-membered carbocyclic group, a 6-membered carbocyclic group, a5-membered heterocyclic group, and a 6-membered heterocyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, and a triazinyl group.

n in Formula 2 may be an integer selected from 0 to 5, and when n is 2or more, rings A₁ may be identical or different. In some embodiments, nin Formula 2 may be 0 or 1.

Ring A₁ may be a ring condensed with two 6-membered rings respectivelypositioned on both sides of ring A₁ by sharing a carbon atom.

When n in Formula 2 is 0, ring A₁ is not present, therefore, the two6-membered rings may be condensed with each other.

In Formula 2, X₁ may be N, C(R₁), or C, X₂ may be N, C(R₂), or C, X₃ maybe N, C(R₃), or C, X₄ may be N, C(R₄), or C, X₅ may be N or C(R₅), X₆may be N or C(R₆), X₇ may be N or C(R₇), and X₈ may be N or C(R₈).

In Formula 2, when X₁ is C, X₁ may bind to (L₁)_(a1), (L₂)_(a2), or(L₃)_(a3), when X₂ is C, X₂ may bind to (L₁)_(a1), (L₂)_(a2), or(L₃)_(a3), when X₃ is C, X₃ may bind to (L₁)_(a1), (L₂)_(a2), or(L₃)_(a3), when X₄ is C, X₄ may bind to (L₁)_(a1), (L₂)_(a2), or(L₃)_(a3), and at least one selected from X₁ to X₄ may be C.

At least one selected from X₁ to X₈ in Formula 2 may be N.

In some embodiments, one, two, or three of X₁ to X₈ in Formula 2 may beN.

In some embodiments, one or two of X₁ to X₈ in Formula 2 may be N, butit is not limited thereto.

In Formula 1, L₁ to L₃ may be each independently selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₁₄ arylene group, a substituted or unsubstitutedC₁-C₁₃ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

In some embodiments, L₁ to L₃ in Formula 1 may be each independentlyselected from

a cyclopentylene group, a cyclohexylene group, a cyclopentenylene group,a cyclohexenylene group, a cycloheptenylene group, a phenylene group, anaphthylene group, a fluorenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, an isoquinolinylene group, aquinoxalinylene group, a quinazolinylene group, a carbazolylene group,an acridinylene group, a phenanthrolinylene group, a phenazinylenegroup, a benzooxazolylene group, a benzoimidazolylene group, afuranylene group, a benzofuranylene group, a thiophenylene group, abenzothiophenylene group, a thiazolylene group, an isothiazolylenegroup, a benzothiazolylene group, an isoxazolylene group, an oxazolylenegroup, a triazolylene group, a tetrazolylene group, an oxadiazolylenegroup, a triazinylene group, a dibenzofuranylene group, adibenzothiophenylene group, an imidazopyrimidinylene group, and animidazopyridinylene group; and

a cyclopentylene group, a cyclohexylene group, a cyclopentenylene group,a cyclohexenylene group, a cycloheptenylene group, a phenylene group, anaphthylene group, a fluorenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, an isoquinolinylene group, aquinoxalinylene group, a quinazolinylene group, a carbazolylene group,an acridinylene group, a phenanthrolinylene group, a phenazinylenegroup, a benzooxazolylene group, a benzoimidazolylene group, afuranylene group, a benzofuranylene group, a thiophenylene group, abenzothiophenylene group, a thiazolylene group, an isothiazolylenegroup, a benzothiazolylene group, an isoxazolylene group, an oxazolylenegroup, a triazolylene group, a tetrazolylene group, an oxadiazolylenegroup, a triazinylene group, a dibenzofuranylene group, adibenzothiophenylene group, an imidazopyrimidinylene group, and animidazopyridinylene group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, animidazopyridinyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group.

In some embodiments, L₁ to L₃ in Formula 1 may be each independentlyselected from

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, an isoquinolinylene group,a quinoxalinylene group, a quinazolinylene group, a furanylene group, abenzofuranylene group, a thiophenylene group, a benzothiophenylenegroup, a thiazolylene group, an isothiazolylene group, an isoxazolylenegroup, an oxazolylene group, an oxadiazolylene group, a triazinylenegroup, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, an isoquinolinylene group,a quinoxalinylene group, a quinazolinylene group, a furanylene group, abenzofuranylene group, a thiophenylene group, a benzothiophenylenegroup, a thiazolylene group, an isothiazolylene group, an isoxazolylenegroup, an oxazolylene group, an oxadiazolylene group, a triazinylenegroup, a dibenzofuranylene group, and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group.

In some embodiments, L₁ to L₃ in Formula 1 may be each independentlyselected from

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group,but they are not limited thereto.

In some embodiments, L₁ to L₃ in Formula 1 may be each independently agroup represented by one of Formulae 5-1 to 5-9, but they are notlimited thereto:

wherein in Formulae 5-1 to 5-9,

Z₁ and Z₂ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, and—Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group;

d1 may be an integer selected from 1 to 4, d2 may be an integer selectedfrom 1 to 3, d3 may be an integer selected from 1 to 6, d4 may be aninteger selected from 1 to 8, and d6 may be an integer of 1 to 5; and

* and *′ each indicates a binding site to a neighboring atom.

a1 to a3 in Formula 1 may be each independently 0, 1, or 2. When a1 is0, -(L₁)_(a1)-*′ in Formula 1 may be a single bond, when a2 is 0,*-(L₂)_(a2)-*′ in Formula 1 may be a single bond, and when a3 is 0,*-(L₃)_(a3)-*′ in Formula 1 may be a single bond. When a1 is 2 or more,groups L₁ may be identical to or different from each other, when a2 is 2or more, groups L₂ may be identical to or different from each other, andwhen a3 is 2 or more, groups L₃ may be identical to or different fromeach other. In some embodiments, a1 to a3 in Formula 1 may be eachindependently 0 or 1.

In Formulae 1 and 2, R₁ to R₉ and R₁₁ to R₁₃ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₁₄ aryl group, a substituted orunsubstituted C₆-C₁₄ aryloxy group, a substituted or unsubstitutedC₆-C₁₄ arylthio group, a substituted or unsubstituted C₁-C₁₃ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and—B(Q₆)(Q₇).

In some embodiments, in Formulae 1 and 2, R₁ to R₉ and R₁₁ to R₁₃ may beeach independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group, each substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenylgroup, a phenyl group, a naphthyl group, a fluorenyl group, a pyrrolylgroup, an imidazolyl group, a pyrazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, abenzoimidazolyl group, a furanyl group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, a benzothiazolyl group, an isoxazolyl group, anoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolylgroup, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, an imidazopyrimidinyl group, an imidazopyridinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group.

In some embodiments, in Formulae 1 and 2, R₁ to R₈ and R₁₁ to R₁₃ may beeach independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein R₉ may be selected from

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group.

In some embodiments, in Formulae 1 and 2, R₁ to R₈ and R₁₁ to R₁₃ may beeach independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein R₉ may be selected from

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group, but they are not limited thereto.

R₁₄ to R₁₆ in Formula 1 may be each independently a group represented byFormula 2.

In some embodiments, R₁₄ to R₁₆ in Formula 1 may be each independentlyselected from a group represented by one of Formulae 2-1 to 2-108:

wherein in Formulae 2-1 to 2-108,

X₉ may be O, S, or N(R₉), and the descriptions for R₁ to R₉ may be thesame as described in the specification.

In some embodiments, in Formulae 2-1 to 2-108, R₁ to R₈ may be eachindependently

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group, each substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenylgroup, a phenyl group, a naphthyl group, a fluorenyl group, a pyrrolylgroup, an imidazolyl group, a pyrazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, abenzoimidazolyl group, a furanyl group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, a benzothiazolyl group, an isoxazolyl group, anoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolylgroup, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, an imidazopyrimidinyl group, an imidazopyridinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein R₉ may be selected from

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group; and

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyrrolyl group, an imidazolyl group, apyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoxazolyl group, a benzoimidazolyl group, a furanyl group, abenzofuranyl group, a thiophenyl group, a benzothiophenyl group, athiazolyl group, an isothiazolyl group, a benzothiazolyl group, anisoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group,a dibenzothiophenyl group, an imidazopyrimidinyl group, and animidazopyridinyl group, each substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenylgroup, a phenyl group, a naphthyl group, a fluorenyl group, a pyrrolylgroup, an imidazolyl group, a pyrazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, abenzoimidazolyl group, a furanyl group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, a benzothiazolyl group, an isoxazolyl group, anoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolylgroup, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, an imidazopyrimidinyl group, an imidazopyridinyl group, abiphenyl group, and a terphenyl group;

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group.

In some embodiments, R₁₄ to R₁₆ in Formula 1 may be each independently agroup represented by one of Formulae 2-1, 2-6, 2-7, 2-19, 2-31, 2-36,2-43, 2-45, 2-47, 2-48, 2-60, 2-63, 2-67, 2-72, 2-80, 2-89, 2-91, 2-93,2-96, and 2-98, but they are not limited thereto.

In some embodiments, in Formulae 2-1 to 2-108,

R₁ to R₈ may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein R₉ may be selected from

a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group, but they are not limited thereto.

In some embodiments, R₁₄ to R₁₆ in Formula 1 may be each independently agroup represented by one of Formulae 3-1 to 3-41, but they are notlimited thereto.

In Formula 1, b1, b3, c1, and c3 may be each independently an integerselected from 1 to 4, and b2 and c2 may be each independently an integerselected from 0 to 3.

b1 indicates the number of R₁₁, and when b1 is 2 or more, groups R₁₁ maybe identical or different from each other. The descriptions for b2 andb3 may be understood by referring to the descriptions for b1 and astructure of Formula 1.

In some embodiments, b1 to b3 in Formula 1 may be each independently 1or 2. In some embodiments, b1 to b3 in Formula 1 may be 1, but they arenot limited thereto.

In Formula 1, c1+c2+c3≥1. In other words, at least one selected from R₁₄to R₁₆ in Formula 1 is essentially present.

In some embodiments, c1 to c3 in Formula 1 may be each independently 0or 1, and c1+c2+c3≥1.

In some embodiments, in Formula 1,

c1 may be 0, c2 may be 1, and c3 may be 0;

c1 may be 0, c2 may be 0, and c3 may be 1;

c1 may be 1, c2 may be 1, and c3 may be 0; or

c1 may be 1, c2 may be 0, and c3 may be 1, but they are not limitedthereto.

In some embodiments, the condensed cyclic compound represented byFormula 1 may be represented by one of Formulae 1A to 1H:

In Formulae 1A to 1H, the descriptions for L₁ to L₃, a1 to a3, R₁₁ toR₁₆, and b1 to b3 may be the same as defined herein.

In some embodiments, in Formulae 1A and 1H, L₁ to L₃ may be eachindependently selected from

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a biphenyl group, and a terphenyl group;

a1 to a3 may be each independently 0 or 1,

R₁₁ to R₁₃ may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and —Si(Q₂₃)(Q₂₄)(Q₂₅); and

—Si(Q₃)(Q₄)(Q₅);

wherein Q₃ to Q₅ and Q₂₃ to Q₂₅ may be each independently selected froma hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group,a naphthyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group,

b1 to b3 may be each independently 0 or 1,

R₁₄ to R₁₆ may be each independently a group represented by one ofFormulae 2-1 to 2-108 (for example, by one of Formulae 3-1 to 3-41).

In some embodiments, the condensed cyclic compound represented byFormula 1 may be represented by one of Formulae 1-1 to 1-10, but it isnot limited thereto:

wherein in Formulae 1-1 to 1-10,

the descriptions for L₁ to L₃, a1 to a3, and R₁₄ to R₁₆ may be the sameas defined herein,

R₁₁ to R₁₃ may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group.

In some embodiments, in Formulae 1-1 to 1-10,

L₁ to L₃ may be each independently a group represented by one ofFormulae 5-1 to 5-9,

a1 to a3 may be each independently 0 or 1,

R₁₄ to R₁₆ may be each independently a group represented by one ofFormulae 2-1 to 2-108 (for example, by one of Formulae 3-1 to 3-41),

R₁₁ to R₁₃ may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a furanylene group, a benzofuranyl group, athiophenyl group, a benzothiophenyl group, a thiazolyl group, anisothiazolyl group, an isoxazolyl group, an oxazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, abiphenyl group, a terphenyl group, and —Si(Q₂₃)(Q₂₄)(Q₂₅);

wherein Q₂₃ to Q₂₅ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group,but they are not limited thereto.

A molecular weight of the condensed cyclic compound represented byFormula 1 may be, for example, in a range of about 300 Da to about 2,000Da. In some embodiments, a molecular weight of the condensed cycliccompound represented by Formula 1 may be, for example, in a range ofabout 348 Da to about 1,500 Da. In some embodiments, a molecular weightof the condensed cyclic compound represented by Formula 1 may be, forexample, in a range of about 348 Da to about 1,000 Da. When a molecularweight of the condensed cyclic compound represented by Formula 1 iswithin the above described range, the condensed cyclic compound may beeasily purified by using a sublimation refining method.

In Formula 1, at least one of substituents of the substituted 5-memberedcarbocyclic group, substituted 6-membered carbocyclic group, substituted5-membered heterocyclic group, substituted 6-membered heterocyclicgroup, substituted C₃-C₁₀ cycloalkylene group, substituted C₁-C₁₀heterocycloalkylene group, substituted C₃-C₁₀ cycloalkenylene group,substituted C₁-C₁₀ heterocycloalkenylene group, substituted C₆-C₁₄arylene group, substituted C₁-C₁₃ heteroarylene group, substituteddivalent non-aromatic condensed polycyclic group, substituted divalentnon-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₁₄ aryl group, substituted C₆-C₁₄ aryloxy group,substituted C₆-C₁₄ arylthio group, substituted C₁-C₁₃ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ arylgroup, a C₆-C₁₄ aryloxy group, a C₆-C₁₄ arylthio group, a C₁-C₁₃heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₄ alkyl group, a C₂-C₁₄alkenyl group, a C₂-C₁₄ alkynyl group, a C₁-C₁₃ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₆-C₁₄aryloxy group, a C₆-C₁₄ arylthio group, a C₁-C₁₃ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇); and

—N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, and Q₂₁ to Q₂₇ may be each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₁-C₁₃heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group.

In Formula 1, the number of rings that are condensed with each other inthe divalent non-aromatic condensed polycyclic group, divalentnon-aromatic condensed heteropolycyclic group, monovalent non-aromaticcondensed polycyclic group, and monovalent non-aromatic condensedheteropolycyclic group may be 2 or 3.

In some embodiments, the condensed cyclic compound may be selected fromCompounds 1 to 68 below.

R₁₄ to R₁₆ in the condensed cyclic compound represented by Formula 1 areeach independently a group represented by Formula 2, and sincec1+c2+c3≥1, the condensed cyclic compound represented by Formula 1essentially includes at least one selected from R₁₄ to R₁₆. Formula 2 isa condensed ring in which a plurality of rings are condensed with eachother. Additionally, at least one selected from X₁ to X₈ in Formula 2 isN, that is, Formula 2 essentially includes N as a ring-forming atom.Moreover, when ring A₁ in Formula 2 includes a hetero atom, the heteroatom is selected from the group consisting of O, S, and N(R₉).Accordingly, the condensed cyclic compound represented by Formula 1 canhave electric characteristics suitable for an organic light-emittingdevice.

Also, the number of rings condensed with each other among the divalentnon-aromatic condensed polycyclic group, the divalent non-aromaticcondensed heteropolycyclic group, the monovalent non-aromatic condensedpolycyclic group, and the monovalent non-aromatic condensedheteropolycyclic group included in the condensed cyclic compoundrepresented by Formula 1 is 2 or 3. Thus, the condensed cyclic compoundcan have excellent thermal stability. For example, the condensed cycliccompound may have a decomposition temperature that is higher than asublimation temperature under a vacuum degree in a range of about 10⁻⁸torr to about 10⁻³ torr. Therefore, the condensed cyclic compound mayprovide excellent manufacturing process efficiency, and an organiclight-emitting device including the same may have improved devicestability when the device is being used, thereby providing a device witha long lifespan.

In addition, the condensed cyclic compound represented by Formula 1 mayhave a relatively low level of the highest occupied molecular orbital(HOMO) energy level as a material for an organic light-emitting device,and a variety of properties may be achieved by substituting asubstituent, thereby having improved charge transporting ability. Inconclusion, an organic light-emitting device employing the condensedcyclic compound represented by Formula 1 may have a high efficiency, lowdriving voltage, high luminance, and long lifespan.

For example, the HOMO energy level, lowest unoccupied molecular orbital(LUMO) energy level, T₁ energy level, and S₁ energy level of theCompounds 1, 2, 4, 5, 6, 9, 17, 35, 48, 54, 63, 65, 67, and 68 weresimulated by using Gaussian. The simulation evaluation results are shownin Table 1:

TABLE 1 HOMO (eV) LUMO (eV) T₁ (eV) S₁ (eV) Compound 1 −5.435 −1.8362.514 3.182 Compound 2 −5.433 −1.888 2.488 3.138 Compound 4 −5.424−2.011 2.414 2.938 Compound 5 −5.401 −1.893 2.557 3.076 Compound 6−5.350 −1.824 2.576 3.031 Compound 9 −5.398 −1.941 2.538 3.108 Compound17 −5.638 −1.844 2.740 3.438 Compound 35 −5.488 −1.777 2.697 3.285Compound 48 −5.440 −1.862 2.724 3.138 Compound 54 −5.387 −1.782 2.7613.167 Compound 63 −5.415 −1.889 2.835 3.178 Compound 65 −5.510 −1.3992.868 3.563 Compound 67 −5.186 −1.284 2.544 3.440 Compound 68 −5.310−1.888 2.423 2.970

Referring to Table 1, it was confirmed that the condensed cycliccompound represented by Formula 1 is suitable for a material to be usedin an organic layer of an organic light-emitting device, for example, inan auxiliary layer or emission layer.

A method of synthesizing the condensed cyclic compound represented byFormula 1 may be understood to one of ordinary skill in the art byreferring to Synthesis Examples described below.

Therefore, the condensed cyclic compound represented by Formula 1 may beappropriate to be used in an organic layer of an organic light-emittingdevice, for example as a host in an emission layer of the organic layer.

Thus, according to another aspect, provided is an organic light-emittingdevice that may include:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and at least onecondensed cyclic compound represented by Formula 1.

Since the organic light-emitting device has an organic layer includingthe condensed cyclic compound represented by Formula 1, the organiclight-emitting device may have a low driving voltage, high efficiency,high luminance, and long lifespan.

The condensed cyclic compound represented by Formula 1 may be includedin between a pair of electrodes of the organic light-emitting device. Insome embodiments, the condensed cyclic compound may be included in atleast one selected from the emission layer, a hole transport region (forexample, including at least one selected from a hole injection layer, ahole transport layer, and an electron blocking layer) disposed betweenthe first electrode and the emission layer, and an electron transportregion (for example, including at least one selected from a holeblocking layer, an electron transport layer, and an electron injectionlayer) disposed between the emission layer and the second electrode. Insome embodiments, the condensed cyclic compound represented by Formula 1may be included in the emission layer. Here, the emission layer mayfurther include a dopant, and the condensed cyclic compound included inthe emission layer may serve as a host. The emission layer may be agreen emission layer that emits green light or a blue emission layerthat emits blue light, and the dopant may be a phosphorescent dopant.

As used herein, the expression the “(organic layer) includes at leastone condensed cyclic compound” may be construed as meaning the “(organiclayer) may include one condensed cyclic compound in a range of Formula 1or two different condensed cyclic compounds in a range of Formula 1”.

For example, the organic layer may include only Compound 2 as thecondensed cyclic compound. In this regard, Compound 2 may be included inthe emission layer of the organic light-emitting device. Alternatively,the organic layer may include Compound 2 and Compound 5 as the condensedcyclic compounds. In this regard, Compound 2 and Compound 5 may beincluded in the same layer (for example, both Compound 2 and Compound 5may be included in the emission layer) or respectively included indifferent layers.

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode. Alternatively, the first electrode may bea cathode, which is an electron injection electrode, and the secondelectrode may be an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, the second electrodemay be a cathode, and the organic layer may include:

i) a hole-transport region disposed between the first electrode and theemission layer, wherein the hole-transport region may include at leastone selected from a hole injection layer, a hole-transport layer, and anelectron blocking layer; and

ii) an electron-transport region disposed between the emission layer andthe second electrode, wherein the electron-transport region may includeat least one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer.

As used herein, the term the “organic layer” refers to a single and/or aplurality of layers disposed between the first electrode and the secondelectrode in an organic light-emitting device. The “organic layer” mayinclude not only organic compounds but also organometallic complexesincluding metals.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, a structure and a method ofmanufacturing the organic light-emitting device according to anembodiment will be described with reference to FIG. 1.

The organic light-emitting device 10 includes a first electrode 11, anorganic layer 15, and a second electrode 19, which are sequentiallylayered in the stated order.

A substrate may be additionally disposed under the first electrode 11 oron the second electrode 19. The substrate may be a conventionalsubstrate that is used in an organic light-emitting device, such asglass substrate or a transparent plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellency.

The first electrode 11 may be formed by vacuum-depositing or sputteringa material for forming the first electrode on the substrate. The firstelectrode 11 may be an anode. The material for the first electrode 11may be selected from materials with a high work function for an easyhole injection. The first electrode 11 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. The materialfor the first electrode 11 may be selected from indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO).Alternatively, a metal such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag).

The first electrode 11 may have a single layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 11 may have a triple-layer structure of ITO/Ag/ITO, butit is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, hole transport layer, electron blocking layer, andbuffer layer.

The hole transport region may only include a hole injection layer or ahole transport layer. Alternatively, the hole transport region mayinclude a structure in which a hole injection layer/a hole transportlayer or a hole injection layer/a hole transport layer/an electronblocking layer are sequentially layered on the first electrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer (HIL) may be formed on the first electrode 11 by usingvarious methods such as vacuum-deposition, spin coating, casting, andLangmuir-Blodgett (LB) method.

A hole injection layer is formed by vacuum-deposition, for example, thevacuum-deposition may be performed at a deposition temperature in arange of about 100° C. to about 500° C., at a vacuum degree in a rangeof about 10⁻⁸ to about 10⁻³ torr, and at a deposition rate in a range ofabout 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, though theconditions may vary depending on a compound that is used as a holeinjection material and a structure and thermal properties of a desiredhole injection layer, but it is not limited thereto.

When a hole injection layer is formed by spin coating, the spin coatingmay be performed at a coating rate in a range of about 2,000 revolutionsper minute (rpm) to about 5,000 rpm, and at a temperature in a range ofabout 80° C. to 200° C. for removing a solvent after the spin coating,though the conditions may vary depending on a compound that is used as ahole injection material and a structure and thermal properties of adesired HIL, but is not limited thereto.

The conditions for forming a hole transport layer and an electronblocking layer may be inferred based on the conditions for forming thehole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, a spiro-TPD, a spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylene groupand a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.

In Formula 201, xa may be each independently an integer selected from 0to 5, and xb may be an integer selected from 0, 1, and 2. In someembodiments, xa may be 1 and xb may be 0, but they are not limitedthereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group (for example, a methyl group, an ethylgroup, a propyl group, a butyl group, a pentyl group, or a hexyl group),and a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxygroup, a propoxy group, a butoxy group, or a pentoxy group);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but they are notlimited thereto.

In Formula 201, R₁₀₉ may be selected from

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group.

According to an embodiment, the compound represented by Formula 201 maybe represented by Formula 201A, but it is not limited thereto:

Descriptions for R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A are the sameas described above.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20, but theyare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes the a hole injection layer and a holetransport layer, a thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, for example, about 100 Å toabout 1000 Å, a thickness of the hole transport layer may be in a rangeof about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500Å. When the thicknesses of the hole transport region, the hole injectionlayer, and the hole transport layer are within these ranges, excellenthole transport characteristics may be obtained without a substantialincrease in driving voltage.

The hole transport region may further include, in addition to thementioned materials above, a charge-generating material to improveconductive properties. The charge-generating material may behomogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but is not limited thereto. Forexample, non-limiting examples of the p-dopant are a quinone derivative,such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and acompound containing a cyano group, such as Compound HT-D1 illustratedbelow, but they are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer toimprove the efficiency of an organic light-emitting device.

An emission layer (EML) may be formed on the hole transport region byusing various methods, such as vacuum-deposition, spin coating, casting,or an LB method. When the emission layer is formed by vacuum-depositionor spin coating, vacuum-deposition and coating conditions for theemission layer may be generally similar to the conditions for forming ahole injection layer, though the conditions may vary depending on thecompound used.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer.Alternatively, the emission layer may have a structure in which the redemission layer, the green emission layer, and/or the blue emission layerare layered to emit white light or other various embodiments arepossible.

The emission layer may include the condensed cyclic compound representedby Formula 1. The emission layer may further include a dopant. Thedopant may include at least one selected from a fluorescent dopant and aphosphorescent dopant.

For example, a host in the emission layer may include the condensedcyclic compound represented by Formula 1.

The dopant in the emission layer may include a fluorescent dopant whichemits light according to a fluorescent emission mechanism or aphosphorescent dopant which emits light according to a phosphorescentemission mechanism.

According to an embodiment, the dopant in the emission layer may be aphosphorescent dopant, and the phosphorescent dopant may include anorganometallic compound represented by Formula 81:

wherein in Formula 81,

M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti),zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium(Tm);

Y₁ to Y₄ may be each independently carbon (C) or nitrogen (N);

Y₁ and Y₂ may be linked to each other via a single bond or a doublebond, and Y₃ and Y₄ are linked to each other via a single bond or adouble bond;

CY₁ and CY₂ may be each independently selected from a benzene, anaphthalene, a fluorene, a spiro-fluorene, an indene, a pyrrole, athiophene, a furan, an imidazole, a pyrazole, a thiazole, anisothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, apyrimidine, a pyridazine, a quinoline, an isoquinoline, abenzoquinoline, a quinoxaline, a quinazoline, a carbazole, abenzoimidazole, a benzofuran, a benzothiophene, an isobenzothiophene, abenzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole,a triazine, a dibenzofuran, and a dibenzothiophene, and CY₁ and CY₂ maybe optionally additionally linked to each other via an organic linkinggroup;

R₈₁ and R₈₂ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

a81 and a82 may be each independently an integer selected from 1 to 5;

n81 may be an integer selected from 0 to 4;

n82 may be an integer selected from 1, 2, and 3;

L₈₁ may be a monovalent organic ligand, a divalent organic ligand, or atrivalent organic ligand.

The phosphorescent dopant may include at least one selected fromCompounds PD1 to PD78 below, but it is not limited thereto:

Alternatively, the phosphorescent dopant may include PtOEP or FIr6below:

The fluorescent dopant may include at least one selected from DPAVBi,BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

When the emission layer includes the host and the dopant, an amount ofthe dopant may be selected from in a range of about 0.01 to about 20parts by weight based on about 100 parts by weight of the host, but theamount is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer, but is not limited thereto.

For example, the electron transport region may have a structure of ahole blocking layer/an electron transport layer/an electron injectionlayer or an electron transport layer/an electron injection layer, but itis not limited thereto. The electron transport layer may have a singlelayer structure or a multi-layer structure including two or moredifferent materials.

The conditions for forming a hole blocking layer, an electron transportlayer, and an electron injection layer may be inferred based on theconditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may, for example, include at least one selected fromBCP, Bphen, and TmPyPB, but it is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within this range, excellenthole blocking characteristics may be obtained without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, Bphen, Alq₃, BAlq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least oneselected from Compounds ET1 and ET2, but it is not limited thereto.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within this range,excellent electron transport characteristics may be obtained without asubstantial increase in driving voltage.

The electron transport layer may further include a metal-containingmaterial in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layer(EIL) that facilitates electron injection from the second electrode 19.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within this range,excellent electron injection characteristics may be obtained without asubstantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for the second electrode 19may be a material having a relatively low work function, such as ametal, an alloy, an electrically conductive compound, and a mixturethereof. Detailed examples of the material for forming the secondelectrode 19 are lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). Alternatively, ITO or IZO may be used to forma transmissive second electrode 19 to manufacture a top emissionlight-emitting device, and such a variation may be possible.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but it is not limited thereto.

A C₁-C₆₀ alkyl group as used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms.Detailed examples thereof are a methyl group, an ethyl group, a propylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup as used herein refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group as used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group as used herein refers to a group formed bysubstituting at least one carbon double bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group as used herein refers to a divalent group having thesame structure as a C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group as used herein refers to a group formed bysubstituting at least one carbon triple bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group and a propenyl group. A C₂-C₆₀ alkynylene group as usedherein refers to a divalent group having the same structure as a C₂-C₆₀alkynyl group.

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalentmonocyclic saturated hydrocarbon group including 3 to 10 carbon atoms.Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as a C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentmonocyclic group including at least one hetero atom selected from N, O,P, and S as a ring-forming atom and 1 to 10 carbon atoms. Detailedexamples thereof are a tetrahydrofuranyl group and atetrahydrothiophenyl group. A C₁-C₁₀ heterocycloalkylene group as usedherein refers to a divalent group having the same structure as a C₁-C₁₀heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group including 3 to 10 carbon atoms and at least one doublebond in the ring thereof, which is not aromatic. Detailed examplesthereof are such as a cyclopentenyl group, a cyclohexenyl group, or acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group as used hereinrefers to a divalent group having the same structure as a C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group including at least one hetero atom selected from N, O,P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least onedouble bond in its ring. Detailed examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as aC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having at least one hetero atomselected from N, O, P, and S as a ring-forming atom and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group as used herein refers to a divalentgroup having a carbocyclic aromatic system having at least one heteroatom selected from N, O, P, and S as a ring-forming atom and 1 to 60carbon atoms. Detailed examples of the C₁-C₆₀ heteroaryl group are apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylenegroup each include a plurality of rings, the plurality of rings may befused to each other.

A C₆-C₆₀ aryloxy group as used herein indicates —OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as used hereinindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group as used hereinrefers to a monovalent group that has two or more rings condensed toeach other, only carbon atoms (for example, the number of carbon atomsmay be in a range of 8 to 60) as ring forming atoms, wherein themolecular structure as a whole is non-aromatic. Detailed examples of thenon-aromatic condensed polycyclic group include a fluorenyl group (threerings of the fluorenyl group are condensed with each other). A divalentnon-aromatic condensed polycyclic group as used herein refers to adivalent group having the same structure as the monovalent non-aromaticcondensed polycyclic group.

A monovalent non-aromatic condensed hetero-polycyclic group used hereinrefers to a monovalent group that has a plurality of rings condensedwith each other, has a hetero atom selected from N, O, P, and S, otherthan carbon atoms (for example, the number of carbon atoms may be in arange of 1 to 60), as ring-forming atoms, wherein the molecularstructure as a whole is non-aromatic. Detailed example of the monovalentnon-aromatic condensed heteropolycyclic group includes a carbazolylgroup (three rings of the carbazolyl group are condensed with eachother). A divalent non-aromatic condensed hetero-polycyclic group asused herein refers to a divalent group having the same structure as themonovalent non-aromatic condensed hetero-polycyclic group.

A biphenyl group used herein refers to a phenyl group substituted withat least one phenyl group.

Hereinafter, a compound and an organic light-emitting device accordingto an embodiment will be described in detail with reference to SynthesisExamples and Examples, however, the inventive concept is not limitedthereto. The wording “B was used instead of A” used in describingSynthesis Examples means that an amount of B used was identical to anamount of A used based on molar equivalence.

EXAMPLE Synthesis Example 1: Synthesis of Compound 2

Synthesis of Intermediate 2-5

10 grams (g) (59.8 millimoles (mmol)) of Intermediate 2-6 and 8.44 g(59.8 mmol) of Intermediate 2-6(1) were dissolved in 200 mL ofdimethylsulfoxide (DMSO). 23.4 g (71.8 mmol) of Cs₂CO₃ was addedthereto, and the mixture was stirred for about 15 hours. 500 mL of waterwas added to the mixture. Thereafter, the mixture was filtered toisolate a solid. The isolated solid was mixed with 300 mL of methylenechloride, and 300 mL of water was added thereto in order to extract anorganic layer. The organic layer organic layer was dried using magnesiumsulfate (MgSO₄), and a solvent was removed by evaporation. The residuewas separated and purified by a silica gel chromatography to obtain12.93 g of Intermediate 2-5 (yield: 75%). The compound thus obtained wasconfirmed by using liquid chromatography-mass spectrometry (LC-MS).

C₁₈H₁₂N₂O₂: M+ 288.09.

Synthesis of Intermediate 2-4

10 g (34.7 mmol) of Intermediate 2-5 was added to 25.16 g (111 mmol) ofSnCl₂.2H₂O in ethanol (EtOH) and was stirred for 8 hours while heatingto maintain 70° C. After the reaction had been completed, the result wasallowed to cool to room temperature. The result, which was concentrated,was added to 300 mL of methylene chloride and 300 mL of NaHCO₃ (aq) toextract an organic layer. The organic layer was dried using MgSO₄, and asolvent was removed by evaporation. The residue was separated andpurified by a silica gel chromatography to obtain 6.27 g of Intermediate2-4 (yield: 70%). The compound thus obtained was confirmed by usingLC-MS.

C₁₈H₁₄N₂: M+ 258.12

Synthesis of Intermediate 2-3

6 g (23.23 mmol) of Intermediate 2-4, 60 mL of acetic acid, and 5 mL ofconc. H₂SO₄ were mixed together, placed in an ice bath, and heated to10° C. A mixture of 150 mL of water and 1.6 g (1 eq) of NaNO₂ was addeddropwise thereto for 20 minutes, and the resulting mixture was stirredfor 10 minutes. The result, which was obtained, was heated to 130° C.,and stirred for 20 minutes. After the reaction had been completed, theresult was allowed to cool to room temperature. 300 mL of water wasadded thereto. Thereafter, a precipitated solid was obtained byfiltration. The precipitated solid was separated and purified by asilica gel chromatography to obtain 4.03 g of Intermediate 2-3 (yield:72%). The compound thus obtained was confirmed by using LC-MS.

C₁₈H₁₁N: M+ 241.09

Synthesis of Intermediate 2-2

3 g (12.43 mmol) of Intermediate 2-3 and 2.21 g (12.43 mmol) ofN-bromosuccinimide (NBS) were dissolved in 100 mL of methylene chlorideand stirred for 15 hours at room temperature. After the reaction hadbeen completed, the result was allowed to come to room temperature. 200mL of methylene chloride and 200 mL of water were added dropwise theretoin order to extract an organic layer. The extracted organic layer wasdried using MgSO₄, and a solvent was removed by evaporation. The residuewas separated and purified by a silica gel chromatography to obtain 2.03g of Intermediate 2-2 (yield: 51%). The compound thus obtained wasconfirmed by using LC-MS.

C₁₈H₁₀BrN: M+ 319.00

Synthesis of Intermediate 2-1

2 g (6.25 mmol) of Intermediate 2-2, 2.4 g (9.37 mmol) ofbis(pinacolato)diboron, 1.84 g (18.74 mmol) of potassium acetate, and0.26 g (0.37 mmol) of Pd(PPh₃)₂Cl₂ were dissolved in 30 mL oftetrahydrofuran (THF), and stirred under reflux at 80° C. for 8 hours.The result was allowed to come to room temperature. The organic layerwas extracted by using 200 mL of methylene chloride and 200 mL of water.The extracted organic layer was dried using MgSO₄. The solvent wasremoved by evaporation. The residue was separated and purified by asilica gel chromatography to obtain 1.8 g of Intermediate 2-1 (yield:79%). The compound thus obtained was confirmed by using LC-MS.

C₂₄H₂₂BNO₂: M+ 367.17

Synthesis of Compound 2

1.8 g (4.9 mmol) of Intermediate 2-1, 1.8 g (4.9 mmol) of Intermediate A(4-([1,1′-biphenyl]-4-yl)-2-bromoquinazoline), 1.96 g (12.25 mmol) ofK₂CO₃, and 0.4 g (0.34 mmol) of Pd(PPh₃)₄ were dissolved in 30 mL of THFand 15 mL of H₂O, and the mixture was stirred under reflux at 100° C.for about 16 hours. After the reaction had been completed, the resultwas washed with methylene chloride and toluene and filtered, therebyisolating a solid. The isolated solid was dissolved in dichlorobenzene(DCB) by reflux. The residue was allowed to be filtered by a silica gelchromatography at a high temperature to remove palladium (Pd), therebyobtaining 1.7 g of Compound 2 (yield: 68%). The compound thus obtainedwas confirmed by using LC-MS.

C₃₈H₂₃N₃: M+ 521.19

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 8.30 (d, 2H), 8.19 (d, 2H), 8.13 (d, 1H),7.85-7.75 (m, 6H), 7.58-7.40 (m, 10H), 7.20 (t, 2H)

Synthesis Example 2: Synthesis of Compound 5

Compound 5 (yield: 62%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate B was used instead of Intermediate Ain synthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and nuclear magnetic resonance (NMR).

C₃₈H₂₃N₃: M+ 521.19

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 8.38 (d, 1H), 8.19 (d, 2H), 8.13 (d, 1H),7.94 (s, 1H), 7.84-7.50 (m, 16H), 7.20 (t, 2H)

Synthesis Example 3: Synthesis of Compound 9

Compound 9 (yield: 70%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate C was used instead of Intermediate Ain synthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₄₄H₂₇N₃: M+ 597.22

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 8.38 (d, 1H), 8.30 (d, 2H), 8.19 (d, 2H),8.13 (d, 1H), 7.94 (s, 1H), 7.84-7.41 (m, 18H), 7.20 (t, 2H)

Synthesis Example 4: Synthesis of Compound 35

Compound 35 (yield: 60%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate 35-6 was used instead of Intermediate2-6 in synthesizing Intermediate 2-5, Intermediate 35-5 was used insteadof Intermediate 2-5 in synthesizing Intermediate 2-4, Intermediate 35-4was used instead of Intermediate 2-4 in synthesizing Intermediate 2-3,Intermediate 35-3 was used instead of Intermediate 2-3 in synthesizingIntermediate 2-2, Intermediate 35-2 was used instead of Intermediate 2-2in synthesizing Intermediate 2-1, and Intermediate 35-1 and IntermediateD were used instead of Intermediate 2-1 and Intermediate A insynthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₃₂H₁₉N₃: M+ 445.16

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 9.29 (d, 1H), 9.10 (d, 1H), 8.50 (d, 1H),8.19 (d, 1H), 7.99-7.89 (m, 5H), 7.77 (d, 1H), 7.75 (d, 2H), 7.50-7.41(m, 6H), 7.20 (t, 1H)

Synthesis Example 5: Synthesis of Compound 54

Compound 54 (yield: 61%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate 35-1 and Intermediate E were usedinstead of Intermediate 2-1 and Intermediate A, respectively, insynthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₄₀H₂₃N₃S: M+ 577.16

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 8.19 (d, 1H), 8.05 (d, 1H), 7.99 (d, 1H),7.93 (d, 1H), 7.89 (s, 2H), 7.84 (d, 2H), 7.77-7.75 (m, 3H), 7.58-7.41(m, 11H), 7.20 (t, 1H)

Synthesis Example 6: Synthesis of Compound 65

Compound 65 (yield: 65%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate F was used instead of Intermediate Ain synthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₂₉H₁₆N₂O: M+ 408.13

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 8.43 (d, 1H), 8.19 (d, 2H), 8.03 (d, 1H),7.82 (d, 1H), 7.76 (s, 1H), 7.65-7.50 (m, 6H), 7.33 (d, 1H), 7.23-7.20(m, 3H)

Synthesis Example 7: Synthesis of Compound 67

Compound 67 (yield: 70%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate G was used instead of Intermediate Ain synthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₄₅H₂₇N₃: M+ 609.22

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 9.00 (d, 2H), 8.43 (d, 1H), 8.30 (d, 1H),8.19 (d, 2H), 8.13 (d, 1H), 7.97 (d, 1H), 7.89 (s, 1H), 7.65-7.50 (m,13H), 7.39 (t, 2H), 7.22-7.20 (m, 3H)

Synthesis Example 8: Synthesis of Compound 68

Compound 68 (yield: 61%) was obtained in the same manner as in SynthesisExample 1 except that Intermediate H was used instead of Intermediate Ain synthesizing Compound 2. The compound thus obtained was confirmed byusing LC-MS and NMR.

C₄₄H₂₅N₃O: M+ 611.20

¹H NMR (CDCl₃, 300 MHz) δ(ppm) 9.02 (d, 2H), 8.95 (d, 1H), 8.30 (d, 1H),8.19 (d, 2H), 8.06 (d, 1H), 7.86-7.84 (m, 3H), 7.70-7.49 (m, 14H), 7.97(d, 1H), 7.89 (s, 1H), 7.65-7.50 (m, 14H), 7.22-7.20 (m, 3H)

Evaluation Example 1: Evaluation on HOMO, LUMO, and Triplets (T1) EnergyLevels

HOMO, LUMO, and T1 energy levels of Compounds 2, 5, 54 to 68, A, B, C,and D were evaluated according to the method indicated in Table 2, andresults thereof are shown in Table 3.

TABLE 2 HOMO energy level A potential (Volts, V) - current (Amperes, A)graph of each compound was evaluation method obtained by using cyclicvoltammetry (CV) (electrolyte: 0.1 molar (M) Bu₄NClO₄/solvent:2-MeTHF/electrode: 3 electrode system (working electrode: GC, referenceelectrode: Ag/AgCl, auxiliary electrode: Pt)). Subsequently, fromreduction onset of the graph, a HOMO energy level of the compound wascalculated. LUMO energy level Each compound was diluted at aconcentration of 1 × 10⁻⁵ M in 2- evaluation methodmethyltetrahydrofuran (2-MeTHF), and an UV absorption spectrum thereofwas measured at room temperature by using a Shimadzu UV-350spectrometer. A LUMO energy level thereof was calculated by using anoptical band gap (Eg) from an edge of the absorption spectrum. T1 energylevel A mixture (each compound was dissolved in an amount of 1 milligram(mg) in 3 evaluation method cubic centimeters (cc) of 2-MeTHF) of2-MeTHF and each compound was loaded into a quartz cell. Subsequently,the resultant quartz cell was loaded into liquid nitrogen (77 Kelvins(K)) and a photoluminescence spectrum thereof was measured by using adevice for measuring photoluminescence. The obtained spectrum wascompared with a photoluminescence spectrum measured at room temperature,and peaks observed only at a low temperature were analyzed to calculateT1 energy levels.

TABLE 3 HOMO (eV) LUMO (eV) T1 energy Compound No. (calc.) (calc.) level(eV) Compound 2 −5.652 −2.203 2.441 Compound 5 −5.561 −1.983 2.591Compound 54 −5.596 −1.972 2.770 Compound 68 −5.602 −2.054 2.413 CompoundA −5.985 −1.975 2.911 Compound B −5.874 −2.512 2.142 Compound C −5.712−1.554 2.971 Compound D −5.623 −1.502 2.892

From Table 3, it is confirmed that the compounds prepared in SynthesisExamples have electric characteristics that are suitable for use as amaterial for forming an organic light-emitting device.

Example 1

A glass substrate, on which an anode having a structure of ITO/Ag/ITO(70/1,000/70 Å) was formed, was cut to a size of 50 millimeters (mm)×50mm×0.7 mm, sonicated in isopropyl alcohol, acetone, and pure water, ineach solvent for 5 minutes, and cleaned by the exposure to ultravioletrays for 30 minutes, and ozone. The glass substrate was mounted on avacuum-deposition apparatus.

2-TNATA was vacuum-deposited on the anode of the glass substrate to forma hole injection layer having a thickness of 600 Angstroms (Å).Subsequently, 4,4′-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,000 Å, thereby forming a hole transportregion.

Thereafter, Compound 54 (a host) and Ir(ppy)₃ (a dopant) (referred to asCompound PD1 herein) were co-deposited at a weight ratio of 91:9 on thehole transport layer to form an emission layer having a thickness of 250Å.

BCP was vacuum-deposited on the emission layer to form a hole blockinglayer having a thickness of 50 Å. Alq₃ was vacuum-deposited on the holeblocking layer to form an electron transport layer having a thickness of350 Å. LiF was vacuum-deposited on the electron transport layer to forman electron injection layer having a thickness of 10 Å, thereby formingan electron transport region.

Mg and Ag were vacuum-deposited on the electron injection layer at aweight ratio of 90:10 to form a cathode having a thickness of 120 Å,thereby completing manufacture of an organic light-emitting device.

Examples 2 to 5 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured according to Examples 2to 5 and Comparative Examples 1 to 4 as in Example 1, except that athickness of the hole transport layer was different for each Exampleaccording to Table 4. As a host and a dopant in forming an emissionlayer, hosts and dopants listed in Table 4 were used for each Example.

Evaluation Example 2: Evaluation of Characteristics of OrganicLight-Emitting Device

A driving voltage, current density, luminance, efficiency, emissioncolor, and lifespan of the organic light-emitting devices manufacturedaccording to Examples 1 to 5 and Comparative Examples 1 to 4 weremeasured by using Kethley SMU 236 and luminance meter PR650, and resultsthereof are shown in Table 4. T₉₇ lifespan in Table 4 indicates a periodof time (hr) taken for the luminance to reach 97% with respect to 100%of an initial luminance of 500 nit.

TABLE 4 Thickness of Driving Current Hole Transport EML Voltage DensityLuminance Efficiency Emission LT₉₇ Layer (Å) Host Dopant (V) (mA/cm²)(cd/m²) (cd/A) color (hr) Example 1 1,000 Compound 54 Ir(ppy)₃ 5.4 106,781 68.4 Green 76 Example 2 1,000 Compound 65 Ir(ppy)₃ 5.8 10 6,35465.7 Green 74 Example 3 1,350 Compound 2 PtOEP 5.8 10 3,754 35.1 Red 116Example 4 1,350 Compound 5 PtOEP 6.0 10 3,121 32.2 Red 110 Example 51,350 Compound 67 PtOEP 5.6 10 3,654 38.1 Red 114 Comparative 1,000Compound A Ir(ppy)₃ 8.5 10 4,231 47.2 Green 37 Example 1 Comparative1,000 Compound C Ir(ppy)₃ 7.0 10 4,712 40.1 Green 32 Example 2Comparative 1,000 Compound D Ir(ppy)₃ 7.7 10 4,552 45.0 Green 35 Example3 Comparative 1,350 Compound B PtOEP 8.2 10 1,786 20.1 Red 51 Example 4

Referring to Table 4, it is confirmed that the organic light-emittingdevices according to Examples 1 and 2 have a low driving voltage, highefficiency, and long lifespan compared to the organic light-emittingdevices according to Comparative Examples 1 to 3, and the organiclight-emitting devices according to Examples 3 and 4 have a low drivingvoltage, high efficiency, and long lifespan compared to the organiclight-emitting devices according to Comparative Example 4.

As described above, according to the one or more of the above exemplaryembodiments, the condensed cyclic compound according to embodiments hasexcellent electric characteristics and thermal stability. Accordingly,an organic light-emitting device including the condensed cyclic compoundmay have a low driving voltage, high efficiency, high luminance, andlong lifespan.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the FIGURES, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope as defined by thefollowing claims.

What is claimed is:
 1. A condensed cyclic compound represented byFormula 1A:

wherein in Formula 1A, L₂ is a phenylene or a naphthylene group, eachoptionally substituted with at least one of a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenylgroup, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, anaphthyl group, Si(Q₂₃)(Q₂₄)(Q₂₅), or any combination thereof, whereinQ₂₃ to Q₂₅ are each independently a hydrogen, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, or a naphthyl group, a2 is 1 or 2,provided that when R₁₅ is of Formulae 2-89, 2-91, 2-93, 2-96 or 2-98,then a2 is 0, R₁₁ to R₁₃ are each independently a hydrogen, a deuterium,F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a phenyl group, anaphthyl group, a C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group; whereinR₁₅ is a group represented by one of Formulae 2-1, 2-7, 2-19, 2-89,2-91, 2-93, 2-96, and 2-98,

wherein in Formulae 2-1, 2-7, 2-19, 2-89, 2-91, 2-93, 2-96, and 2-98, X₉is O, S, or N(R₉), R₁ to R₈ are each independently a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, phenyl,biphenyl, terphenyl, a C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group;wherein R₉ is a phenyl or a naphthyl group, each optionally substitutedwith at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C1-C₂₀ alkyl group, a C1-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, or any combination thereof; b1 and b3 are each independently aninteger selected from 1 to 4, b2 is an integer selected from 0 to
 3. 2.The condensed cyclic compound of claim 1, wherein when present, L₂ is aphenylene group or a naphthylene group, each optionally substituted withat least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, —Si(Q₂₃)(Q₂₄)(Q₂₅), or any combination thereof; whereinQ₂₃ to Q₂₅ are each independently a hydrogen, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, or anycombination thereof.
 3. The condensed cyclic compound of claim 1,wherein the R₁₅ is a group represented by one of Formulae 3-1 to 3-5,3-13 to 3-21, 3-24 to 3-25, 3-34 to 3-35, and 3-38 to 3-39:


4. The condensed cyclic compound of claim 1, wherein the condensedcyclic compound is represented by one of Formulae 1-1, 1-3, and 1-4:

wherein in the Formulae 1-1, 1-3, and 1-4, the descriptions for L₂, a2,R₁₁, R₁₃, and R₁₅ are the same as in claim
 1. 5. An organiclight-emitting device comprising: a first electrode; a second electrode;and an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer comprises an emission layer and atleast one condensed cyclic compound represented by Formula 1 of claim 1.6. The organic light-emitting device of claim 5, wherein the emissionlayer comprises the at least one condensed cyclic compound of claim 1.7. The organic light-emitting device of claim 6, wherein the firstelectrode is an anode, the second electrode is a cathode, and theorganic layer comprises: i) a hole transport region disposed between thefirst electrode and the emission layer, wherein the hole transportregion comprises at least one selected from the group consisting of ahole injection layer, a hole transport layer, and an electron blockinglayer, and ii) an electron transport region disposed between theemission layer and the second electrode, wherein the electron transportregion comprises at least one selected from the group consisting of ahole blocking layer, an electron transport layer, and an electroninjection layer.
 8. The organic light-emitting device of claim 6,wherein the emission layer further comprises a phosphorescent dopant,and wherein an amount of the at least one condensed cyclic compound ofclaim 1 in the emission layer is greater than an amount of thephosphorescent dopant.
 9. A condensed cyclic compound selected from thegroup consisting of: